Biochemical synthesis of uniformly ¹³C-labeled diterpene hydrocarbons and their bioconversion to diterpenoid phytoalexins in planta

References

• VanEtten HD, Mansfield JW, Bailey J, et al. Two classes of plant antibiotics: phytoalexins versus phytoanticipins. Plant Cell. 1994;6:1191–1192.10.1105/tpc.6.9.1191
   PubMed Web of Science ®Google Scholar
• Dixon RA. Natural products and plant disease resistance. Nature. 2011;411:843–847.
   Web of Science ®Google Scholar
• Nozaki H, Hayashi K, Nishimura N, et al. Momilactone A and B as allelochemicals from moss hypnum plumaeforme: first occurrence in bryophytes. Biosci Biotechnol Biochem. 2007;71(12):3127–3130.10.1271/bbb.70625
   PubMed Web of Science ®Google Scholar
• Miyamoto K, Fujita M, Shenton MR, et al. Evolutionary trajectory of phytoalexin biosynthetic gene clusters in rice. Plant J. 2016;87(3):293–304.10.1111/tpj.2016.87.issue-3
   PubMed Web of Science ®Google Scholar
• Otomo K, Kanno Y, Motegi A, et al. Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A–F in rice. Biosci Biotechnol Biochem. 2004;68(9):2001–2006.10.1271/bbb.68.2001
   PubMed Web of Science ®Google Scholar
• Okada K, Kawaide H, Miyamoto K, et al. HpDTC1, a stress-inducible bifunctional diterpene cyclase involved in momilactone biosynthesis, functions in chemical defence in the moss Hypnum plumaeforme. Sci Rep. 2016;6:25316.10.1038/srep25316
   PubMed Web of Science ®Google Scholar
• Cho EM, Okada A, Kenmoku H, et al. Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor. Plant J. 2004;37:1–8.10.1046/j.1365-313X.2003.01926.x
   PubMed Web of Science ®Google Scholar
• Kanno Y, Otomo K, Kenmoku H, et al. Characterization of a rice gene family encoding type-A diterpene cyclases. Biosci Biotechnol Biochem. 2006;70(7):1702–1710.10.1271/bbb.60044
   PubMed Web of Science ®Google Scholar
• Peters RJ. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry. 2006;67(21):2307–2317.10.1016/j.phytochem.2006.08.009
   PubMed Web of Science ®Google Scholar
• Toyomasu T. Recent advances regarding diterpene cyclase genes in higher plants and fungi. Biosci Biotechnol Biochem. 2008;72(5):1168–1175.10.1271/bbb.80044
   PubMed Web of Science ®Google Scholar
• Okada K. The biosynthesis of isoprenoids and the mechanisms regulating it in plants. Biosci Biotechnol Biochem. 2011;75(7):1219–1225.10.1271/bbb.110228
   PubMed Web of Science ®Google Scholar
• Schmelz EA, Huffaker A, Sims JW, et al. Biosynthesis, elicitation and roles of monocot terpenoid phytoalexins. Plant J. 2014;79(4):659–678.10.1111/tpj.2014.79.issue-4
   PubMed Web of Science ®Google Scholar
• Sugai Y, Miyazaki S, Mukai S, et al. Enzymatic total synthesis of gibberellin A4 from acetate. Biosci Biotechnol Biochem. 2011a;75(1):128–135.10.1271/bbb.100733
   PubMed Web of Science ®Google Scholar
• Ingram TJ, Reid JB. Internode length in pisum: gene na may block gibberellin synthesis between ent-7alpha-hydroxykaurenoic acid and gibberellin A12-aldehyde. Plant Physiol. 1987;83(4):1048–1053.10.1104/pp.83.4.1048
   PubMed Web of Science ®Google Scholar
• Shimane M, Ueno Y, Morisaki K, et al. Molecular evolution of the substrate specificity of ent-kaurene synthases to adapt to gibberellin biosynthesis in land plants. Biochem J. 2014;462(3):539–546.10.1042/BJ20140134
   PubMed Web of Science ®Google Scholar
• Sugai Y, Ueno Y, Hayashi K, et al. Enzymatic (13)C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii. J Biol Chem. 2011b;286(50):42840–42847.10.1074/jbc.M111.302703
   PubMed Web of Science ®Google Scholar
• Shimizu T, Jikumaru Y, Okada A, et al. Effects of a bile acid elicitor, cholic acid, on the biosynthesis of diterpenoid phytoalexins in suspension-cultured rice cells. Phytochemistry. 2008;69:973–981.10.1016/j.phytochem.2007.10.005
   PubMed Web of Science ®Google Scholar
• Swaminathan S, Morrone D, Wang Q, et al. CYP76M7 is an ent-cassadiene C11alpha-hydroxylase defining a second multifunctional diterpenoid biosynthetic gene cluster in rice. Plant Cell. 2009;21(10):3315–3325.10.1105/tpc.108.063677
   PubMed Web of Science ®Google Scholar
• Wang Q, Hillwig ML, Okada K, et al. Characterization of CYP76M5-8 indicates metabolic plasticity within a plant biosynthetic gene cluster. J Biol Chem. 2012;287(9):6159–6168.10.1074/jbc.M111.305599
   PubMed Web of Science ®Google Scholar
• Kitaoka N, Wu Y, Xu M, et al. Optimization of recombinant expression enables discovery of novel cytochrome P450 activity in rice diterpenoid biosynthesis. Appl Microbiol Biotechnol. 2015;99(18):7549–7558.10.1007/s00253-015-6496-2
   PubMed Web of Science ®Google Scholar